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Preparation of pyrrole and pyrrolin fused ring compound with insecticidal activity and use thereof

A technology of compound and alkyl, applied in the field of pesticides, can solve the problems of narrow insecticidal spectrum, limit the selectivity of insect pest control medication, restrict the development of compounds, etc., and achieve the effect of significant insecticidal activity and broad insecticidal spectrum

Inactive Publication Date: 2013-01-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, due to the serious resistance problem caused by the excessive and frequent use of imidacloprid and the cross-resistance between neonicotinoid insecticides due to structural similarity, the application of this type of compound is limited to a certain extent, and it has become a constraint on this field. Important Issues in Compound-like Development
At the same time, neonicotinoid insecticides are mainly effective against Homoptera and Coleoptera pests, and their relatively narrow insecticidal spectrum also limits the selection of insecticides in pest control.

Method used

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  • Preparation of pyrrole and pyrrolin fused ring compound with insecticidal activity and use thereof
  • Preparation of pyrrole and pyrrolin fused ring compound with insecticidal activity and use thereof
  • Preparation of pyrrole and pyrrolin fused ring compound with insecticidal activity and use thereof

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preparation example Construction

[0109] The preparation method of the compound of the present invention

[0110] The compound represented by the general formula (A) of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactant, solvent, base, compound used, reaction temperature, reaction time required, etc. are not limited to the following explanations . The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0111] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at a reaction temperature of 0°C to 60°C (preferably 25°C and 60°C). The reaction time is usually 0.1-24 hours, preferably 0.5-3 hours.

[0112] Protonic acids or Lewis acids used in the reac...

Embodiment 1-45

[0136] Example 1-45: Preparation of pyrrole and dihydropyrrole-fused ring neonicotinoids

Embodiment 1

[0138] 1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrole[1,2-a]imidazole- Synthesis of 5,6-diol (compound I-1)

[0139]

[0140] Add 20ml of dichloromethane to 1.270g (5.0mmol) of 2-chloro-5-((2-(nitromethylene)imidazolin-1-yl)methyl)pyridine, and slowly add 1.270g ( 5.5mmol) of methylglyoxal in water. After reacting at room temperature for 1 hour, let stand, filter the precipitated solid with suction, wash the filter cake with a small amount of dichloromethane and acetone, and dry to obtain the pure product as a white powdery solid with a yield of 85%. Mp=158.3-158.9°C; 1 H NMR (400Mz, DMSO-d 6 ): δ8.40 (d, J = 1.6Hz, 1H), 7.83 (dd, J 1 =8.0Hz,J 2 =2.0Hz, 1H), 7.56(d, J=8.0Hz, 1H), 6.18(s, 1H), 5.48(d, J=6.0Hz, 1H), 5.37(d, J=15.2Hz, 1H), 5.08(d, J=15.2Hz, 1H), 4.68(d, J=6.0Hz, 1H), 3.93-3.84(m, 1H), 3.80(q, J=10.4Hz, 1H), 3.43-3.36(m , 2H), 1.28(s, 3H)ppm; 13 C NMR (100Mz, DMSO-d 6 ): δ160.1, 150.1, 149.8, 139.9, 132.5, 124.8, 108.5,...

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Abstract

The invention provides preparation of a pyrrole and pyrrolin fused ring compound with insecticidal activity and use of the pyrrole and pyrrolin fused ring compound with insecticidal activity. Specifically, the invention relates to a compound (shown as the following formula) with the general formula (A) or the optical isomer, the cis-trans-isomer or the agriculturally pharmaceutically acceptable salt of the compounds, and a preparation method of the compound. The invention further relates to an agricultural composite containing the compound, or the optical isomer, the cis-trans-isomer or the agriculturally pharmaceutically acceptable salt of the compound and the use of the agricultural composite. The compound and the derivative of the compound are high in insecticidal activity to agriculture and forestry pests with the same mecoptera, lepidoptera and the like such as the aphid, the plant hopper, the aleyrodid, the leafhopper, the thrips, the cotton bollworm, the cabbage caterpillar, the plutella xylostella, the prodenia litura, the armyworm and the like.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a preparation method and application of pyrrole and dihydropyrrole fused-ring neonicotinoid pesticides. technical background [0002] The alkaloid nicotine from tobacco leaf extract is a natural insecticide that acts on postsynaptic nicotinic acetylcholine receptors (nAChRs). For a long time, researchers have been using natural nicotine as the leading compound to find and discover new compounds with insecticidal activity that are similar in structure to nicotine and have the same mechanism of action. In the mid-1980s, Bayer developed the first neonicotinoid insecticide, imidacloprid, and became one of the most successful new insecticides. High activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties, appropriate field stability and environmental friendliness have become an important hotspot for the creation of new pesticides. Later, a s...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D401/12C07D417/12C07D405/12A01N43/90A01N43/40A01N43/78A01N43/36A01P7/04
CPCC07D401/12A01N43/78A01N43/90C07D405/12A01N43/36C07D417/12C07D487/04A01N43/40
Inventor 李忠徐晓勇叶振君钱旭红邵旭升须志平曾步兵宋恭华
Owner EAST CHINA UNIV OF SCI & TECH
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